Date of Award
Doctor of Philosophy (PhD)
Chemistry & Biochemistry
The main aim of the research focuses on the study of self-assembly and gelation by several classes of simple sugar derivatives and the potential applications of them as drug delivery vehicles. Since carbohydrates are naturally abundant renewable resources and are therefore readily available and many of them are inexpensive compared to other raw materials. They are also biocompatible which makes them suitable for a wide variety of applications. Combining the use of carbohydrates with low molecular weight gelators (LMWGs) we can introduce a new class of soft materials that are able to self-assemble into spheres, fibers, sheets, and micelles in a wide variety of solvents. The self-assembly occurs through non-covalent forces such as hydrogen bonding, π-π stacking, and van der Waals forces. The entrapment of the solvent in the fibrous network results in a gel formation. There are many applications for these soft materials such as drug delivery, environmental clean-up, and even for reaction catalysis. Previously, our lab has reported that several series of 4,6-O-benzylidene protected D-glucose and N-acetyl-D-glucosamine are effective molecular gelators. In order to probe the effect whether the benzylidene functional group is a structural requirement for gelation, in this research, the phenyl group was replaced with aliphatic functional group. Therefore, a series of 4,6-O-alkylidene protected N-acetyl-D-glucosamine and α-D-methyl glucoside were synthesized and their gelation properties were studied. Depending on the structures of these derivatives, effective LMWGs in aqueous and organic solvents were obtained. The effective hydrogelators obtained from this study were used as drug delivery carriers for naproxen etc. The release profiles of naproxen from the gel-drug matrix were studied carefully using UV-vis spectroscopy. Different methods of preparing the gel with the model drugs were also studied and compared. Several covalently linked drug-gelator conjugates were synthesized and analyzed in the attempt of designing prodrug-based drug delivery systems.
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Bashaw, Kristen E..
"Synthesis, Characterization, and Drug Delivery Applications of Carbohydrate Based Low Molecular Weight Gelators"
(2019). Doctor of Philosophy (PhD), Dissertation, Chemistry & Biochemistry, Old Dominion University, DOI: 10.25777/ff1h-nb19